Triethylamine → {-4-[3-(6-bromo-pyridin-2-yl)-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1809703Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:37][C:38]([O:41][C:42]([NH:44][CH:45]1[CH2:50][CH2:49][CH:48]([NH2:51])[CH2:47][CH2:46]1)=[O:43])([CH3:40])[CH3:39].CCN(CC)CC>CC(O)C>[C:38]([O:41][C:42](=[O:43])[NH:44][CH:45]1[CH2:46][CH2:47][CH:48]([NH:51][C:13]2[N:12]=[C:11]3[N:10]([C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:9]=[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=4)[C:16]3=[CH:15][N:14]=2)[CH2:49][CH2:50]1)([CH3:40])([CH3:37])[CH3:39]

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 3-(6-bromo-pyridin-2-yl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine (from Example 34 supra) (3.8 g, 6.89 mmol), tert-butyl (1r,4r)-4-aminocyclohexylcarbamate (1.8 g, 8.40 mmol) and Et3N (1.2 mL, 8.3 mmo,) in IPA (80 mL) was stirred at 90° C. for 15 hours. The reaction was cooled to room temperature and the precipitate was collected by filtration to give {-4-[3-(6-bromo-pyridin-2-yl)-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as white powder. (Yield 1.5 g, 30%).

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-d316ce855a704dec89459f833a2256a8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362023B2

Reaction notes

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